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Chemical Studies on Marine Biotoxins

Research Project

Project/Area Number 01470128
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionNagoya University

Principal Investigator

ISOBE Minoru  Nagoya University, School of Agriculture, Associate Professor, 農学部 助教授 (00023466)

Co-Investigator(Kenkyū-buntansha) NISHIKAWA Toshio  Nagoya University, School of Agriculture, Assistant Professor, 農学部, 助手 (90208158)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥5,800,000 (Direct Cost: ¥5,800,000)
Fiscal Year 1990: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1989: ¥4,900,000 (Direct Cost: ¥4,900,000)
KeywordsBiotoxins / DSP activity / Okadaic acid / Puffer poison / Tetrodotoxin / Cyclic guanidine / Cancer Promoter / Inhibitor of protein phosphatase / 生物トキンン / 下痢性貝毒
Research Abstract

In the field of Biotoxins, the structral, analytical and synthetic studies on marine toxin are one of the significant subjects. The project has been separated into two parts, involving two natural product, okadaic acid and tetrodotoxin directed toward the basic research. Okadaic acid was known to have DSP activity, and to have inhibitory activity against protein phoshatase. We have synthesized the East Half molecule (EHOK) of O-Kadaic Acid and compared the biological activity of EHOK with okadaic acid itself. EHOK showed no activity (less than 1/100) to protein phosphatase when examined by Prof. Takai, a colaborator. EHOK, however, showed a strong binding activity with antibody of OKA, which was designed for DSP detection. Prof. Yasumoto reported us that EHOK binded in fact, 8 times as strongly as OKA. These two independent biological result with OKA partial analog suggested the okadaic acid molecule is recognized by those system with a different part in its molecule.
In the synthetic works on Tetrodotoxin (TTX), we have concluded the synthesis of a molecule with cyclic guanidine of TTX. Since we have previously reported the cyclohexane moiety, the current target was the combination of the two. Starting from the pyrolysate of cellulose, we use its bromoderivative for Diels-Alder cycloaddition. The unstable bromo-ketone was converted into the stable vinyl phosphate, which was promising for promoting total synthesis of TTX. Further bioorganic studies will be continued.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] M.Isobe: "Synthetic Studies on(ー)ーTetrodotoxin(3)ーーーNitrogenation through Overman Rearrangement and Guanidine Ring Formation." Tetrahedron Letters. 31. 3327-3330 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Isobe: "Methodology for Stereochemical Control in Bioactive Natural Product SynthesisーーーNew Methods toward Enediyne Antitumor Antibiotics" Pure and Applied Chemistry. 62. 2007-2021 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Isobe: "Asymmetric Synthesis via Heteroconjugate AdditionーーーValinol Template as Oxazolidine Heteroolefin vs Acetylenic Nucleophiles" Tetrahedron Letters. 31. 5499-5502 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] A.Herunsalee: "Diastereoselective Heteroconjugate Addition using Phenylthioーacetylnen" Synlett. 701-703 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T.Nishikawa: "Silyl and Tin Acetylene as Nucleophile toward Acyliminium Cation,a Plausible Key Reaction for Dynemicin, Enediyne Antitumor Antibiotic" Synlett. 99-101 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] A.Herunsalee: "Stereoselective Synthesis directed toward Polyoxygenated Compounds,Synthesis of A KDN Equivalent" Synlett. 199-200 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Isobe: "New Synthetic Method using Heteroatom Groups for Stereocontrol in the Total Synthesis of a Marine Polyether Toxin,Okadaic Acid,New trends in Organometallic Chemistry" Hideki Sakurai, 14 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Isobe: "Ansamacrolides Recent Progress in the Chemical Synthesis of Abtibiotics" G.Lukacs,M.Ohono, 31 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Minoru Isobe: "Synthetic studies on (-)-Tetrodotoxin (3) --- Nitrogenation through Overman Rearrangemant and Guanidine Ring Formation." Tetrahedron Letters,. 31. 3327-3330 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Minoru Isobe: Pure and Applied Chemistry,. 62. 2007-2021 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Minoru Isobe: "Asymmetric Synthesis via Heteroconjugate Addition --- Balinol Template as Oxazolidine Heteroolefin vs Acetylenic Nucleophiles." Tetrahedron Letters,. 31. 5499-5502 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] A. Herunsalee: "Diastereoselective Heteroconjugate Addition using Phenylthioacetylene." Synlett. 701-703 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T. Nishikawa: "Silyl and Tin Acetylene as Nucleophile toward Acyliminium Cation, a Plausible key Reaction for Dynemicin, Enediyne Antitumor Antibiotic." Synlett. 99-101 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] A. Herunsalee: "Stereoselective Sythesis directed toward Polyoxygenated Compounds, Sythesis of A KDN Equivalent." Synlett,. 199-200 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Minoru Isobe: "New Synthetic Method using Heteroatom Groups for Stereocontrol in the Total Synthesis of a Marine Polyether Toxin, Okadaic Acid." New trends in Organometallic Chemistry,. 356-369 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Minoru Isobe: "Ansamacrolides" Recent Progress in the Chemical Synthesis of Antibiotics,. (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 8ethodology for Stereochemical Control in Bioactive Natural Product Synthesis --- New Methods toward: nediyne Antitumor Antibiotics.,

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Isobe: "Synthetic Studies on (ー)ーTetrodotoxin (3) ーーーNitrogenation through Overman Rearrangement and Guanidine Ring Formation." Tetrahedron Letters. 31. 3327-3330 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Isobe: "Methodology for Stereochemical Control in Bioactive Natural Product Synthesis ーーー New Methods toward Enediyne Antitumor Antibiotics" Pure and Applied Chemistry. 62. 2007-2021 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Isobe: "Asymmetric Synthesis via Heteroconjugate Addition ーーー Valinol Template as Oxazolidine Heteroolefin vs Acetylenic Nucleophiles" Tetrahedron Letters. 31. 5499-5502 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] A.Herunsalee: "Diastereoselective Heteroconjugate Addition using Phenylthioacetylnen" Synlett. 701-703 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Nishikawa: "Silyl and Tin Acetylene as Nucleophile toward Acyliminium Cation,a Plausible Key Reaction for Dynemicin,Enediyne Antitumor Antibiotic" Synlett. 99-101 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] A.Herunsalee: "Stereoselective Synthesis directed toward Polyoxygenated Compounds,Synthesis of A KDN Equivalent" Synlett. 199-200 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Isobe(分担執筆): "New Synthetic Method using Heteroatom Groups for Stereocontrol in the Total Synthesis of a Marine Polyether Toxin,Okadaic Acid,New trends in Organometallic Chemistry" Hideki Sakurai, 14 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Isobe(分担執筆): "Ansamacrolides Recent Progress in the Chemical Synthesis of Abtibiotics" G.Lukacs,M.Ohono, 31 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Duangchan Uyakul,M.Isobe,T.Goto: "Mycotoxin Analysis by means of tandem Mass spectrometry" J.Assoc.Off.Anal.Chem.72. 491-497 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Duangchan Uyakul,M.Isobe,T.Goto: "FAB Tandem Mass spectra of Aflatoxins,Sterigmatocystin and their analogs" J.of Mycotoxins(Japan). 29. 13-19 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Isobe,D.Uyakul,T.Goto: "FAB-MS/MS spectrometry in Determining γ-Glutamyl Containing Peptides." Agric.Biol.Chem.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Isobe,Y.Fukada,S.Pikul,T.Nishikawa,P.Chabert,T.Goto: "“Stereocontrol in the Bioactive Natural Product Sysnthesis Studies on Tetrodotoxin"NATURAL PRODUCT,Ed.by Radoslav Vlahov" Bulgarian Academy of Sciences, (1990)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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